Penny wants to dump her winker boyfriend, Reed, but must wait until they are outside the breakup window. The "breakup window" is that period of time around holidays and major events when you simply can't dump someone. Penny will just have to wait until after Valentine's Day before giving Reed the heave-ho.
Dave is preparing a five-course romantic meal for his girlfriend, Lindsay. She's been affectionately nicknamed the "crazy sex girl." Dave can only imagine what Lindsay will do to him on the most love-drenched day of the year. Too bad Penny has him believing his lady is just stringing him along because of the break-up window.
Thinking his girl is about to send him to Dumpsville, Dave ditches all his romantic plans. As it turns out, Lindsay had no intention of breaking up with him. In fact, she was planning on giving him his dream gift—a threesome with her hot friend. Dave begs for forgiveness, but the breakup window has closed.
Brad has some Valentine's surprises in store for Jane. Of course, he must reveal all his plans to his wife because she tends to react harshly to unexpected initiatives. We won't go into details. Let's just say Mace is typically involved.
Brad heads down to the dentist to get his teeth polished for his lady. He's never had a cavity until now. Guess that's why he was so unprepared for the aftershocks of nitrous oxide. A super-loopy Brad simply cannot fulfill all those already-revealed surprises he had in store for Jane.
Alex loves Valentine's Day. She's completely up to speed on the entire history of the saint who helps others find love. Alex hopes this will ring true for her as she attends "Captain Danny's Balls to the Wall V-day Keg Race" bash. Sadly, her grandmother's lucky dress and fur make her look like a prostitute. And that's why she gets arrested for solicitation on the way to the party.
Once Alex is sprung from her holding cell, she joins Max as he makes a Valentine's Day limo pickup. One of his passengers happens to be his ex-boyfriend, Grant. They broke up exactly one year ago. Apparently, Max took Grant for granted.
Nobody's Valentine's Day is turning out as planned. Penny is shocked when Reed breaks up with her. Dave is also in the dumps after being dumped. Brad is still high as a kite and referring to his "friends" as Ross (Dave), Rachel (Alex), Phoebe (Penny) and fat Joey (Max). He calls his wife as Monica. So, that must make him Chandler.
Alex believes one of her friends is going to find love on Valentine's Day. With Extreme's "More Than Words" playing in the background, Max makes a sweet apology to Grant by candlelight. That's because he set up dozens of candles on his ex's front porch. The two men share a kiss as they head off to fulfill all those plans Brad had made for Jane. Happy Valentine's Day!